Hello, Internet! Welcome to Ask Dr. NerdLove, the only dating advice column that represents the last, best hope for peace in our galaxy.


This week, it’s all about the woulda, coulda, and shoulda and how to deal with the ones that got away. Yes, the bird in the hand and all that, but if it seems like there’s the chance at an even better option right in front of you? And what about when it seems like you have the opportunity for a second chance with your ex?

It’s time for some tough decisions and some tough love. Let’s do this.


Heya Doc,

I’m engaged to a girl who I love, but I’m IN love with my best friend. The devil is in the details, though, so I guess I should explain.

Let’s start with my fiance, H - she’s a great girl. We have a healthy relationship, we rarely fight and we support each other as best as we can. She came into my life when I needed someone and she has been there for me ever since. It’s not a passionate relationship, but I love H.

Now, for my best friend, K. We’ve known each other since we were 11 years old and there has always been romantic tension between us (I thought it was just on my end, she thought it was just on hers) but we never acted on it. Almost 2 decades of friendship and being in love with each other and neither one of us ever did anything about it. The timing was always “off” - either she was dating (or married to) someone else or I was. But we’ve always kept in touch, we’ve always been close, and we are each other’s missing halves.

Unfortunately, K waited until I was engaged to finally admit her feelings for me, and I wasn’t about to lie to her about my feelings, so we both came clean about 6 months ago. Since then, it has put a strain on my relationships with both women. H doesn’t trust me around my best friend (even though I’ve clearly set boundaries) and K is doing everything she can to NOT cross any boundaries, though I’ve had to stop her from kissing me on a couple of occasions. I can easily say that stopping her from kissing me is the most difficult thing I have ever done.

Some background on the women and history involved in this situation - K and I have both been divorced due to the other partner cheating, so it’s something that we would never do (but I’ve REALLY been tempted to lately). We share similar interests - to the point that it becomes almost creepy. We’ve both had our share of dating and relationships and we’re both tired of trying to find someone.

H is younger and more inexperienced, but she is exceptionally mature for her age. She works hard, is in school to be a veterinarian, and she is financially independent. She treats me very well, and I treat her very well. We support each other as much as we can. But she is still a bit emotionally fragile - she has a history of men using her and leaving her. Our relationship is the first truly healthy relationship she has ever had - and we’re over 2 years in.

Now it seems to be decision time. Should the Stoic in me be happy with my 2-year relationship, appreciate H and accept that if it ends K will be there for me like she has been since I was 11? Or should I do the thing I fear and give up on a healthy relationship (something I’ve never had) to pursue a love I’ve felt for well over half of my life?

It seems to be a toss of the dice to me. I’m a bit stuck, here. Any advice would be appreciated.


-Heart at War

You’re in a shitty place, HaW, and one without any “good” answers. You’re going to need to do some serious soul-searching to figure out what’s right for you. But before you make any serious decisions, let’s look at what you’ve got on both sides.

Let’s start with your fiancé, H, and your relationship with her. It’s stable, it’s healthy but it’s not the most passionate. Passion is a great part of a relationship and it can be important, but it’s not a foundation for a relationship. Passion is exciting but it’s also not an indication of a relationship to last the ages; you can be passionate for someone who is absolutely wrong for you. Just because the two of you burn up the sheets and can’t keep your hands off each other doesn’t mean that you can work together when it counts and the chips are down.


Similarly, passion ebbs and flows in every relationship. In every long-term relationship, passion eventually subsides. It’s called the Coolidge effect; we don’t get the same shot of dopamine to the brain from sex with the same person after a while. This isn’t a good thing or a bad thing; it’s just part of being a mammal. It does, however, tend to correspond with the relationship becoming more emotionally intimate.

Now on the other hand, you have K. K’s been someone you’ve had serious pantsfeelings for since forever (and vice-versa) and your story has been one of “right person, wrong time” for as long as you’ve known each other. But even with that case of constant bad timing, the two of you have managed to stay close and keep your friendship going for more than 20 years. That’s pretty damn impressive and says a lot about the quality of the connection the two of you have.



Now under normal circumstances, I’d say “go forth and finally take your chance with K” and advise you to try not to let the strains of the Throne Room theme from Star Wars distract you two when you both finally hook up now that it seems like your lives have finally aligned…

Except for the part where, y’know, you’re engaged to H. That’s pretty firmly in the “wrong time” scenario. I’m also not entirely thrilled with the fact that K decided to finally tell you how she felt after you got engaged. If K had written in to ask about whether to tell her newly engaged crush how she felt, I’d tell her to back off. I know movies and pop-culture tell us that everything’s forgiven in the name of True Lurve, but it’s incredibly selfish and unfair to sit on those feelings only to drop them on somebody when they’ve committed to somebody else. It’s not just about the two of you now; there’s also that third person in the mix. Now K’s just dragged H into your mix and everything’s fucked up.

So, yeah. That’s really not cool of her to do. And it’s not cool of you to be putting yourself in the position of hurting H. To be sure, it’s ok to have a crush on somebody when you’re involved with someone else, even to spend time with your crush. But right now, you’re playing with fire. This isn’t an ex you have some unresolved feelings for, this is someone who seems to have a hard time respecting certain boundaries (like not kissing the engaged guy)... and someone youre having a hard time enforcing those boundaries around.


That, my friend, is a recipe for disaster and broken hearts—H’s for sure, quite likely yours and probably K’s for good measure. Don’t forget, no matter how hot for each other you two may be, if you hook up before thing are finished between you and H, then both you and K are going to be having to deal with the guilt and shame that comes with being the cheater. That could very well sink any burgeoning relationship the two of you might have.

So until you’ve made your decision, you need to be the one to pump the brakes. This means no putting yourself in positions where you have the opportunity for “mistakes” to happen with K - especially mistakes that you want to happen. It just takes one opportune moment of weakness after all. I’m not saying you can’t see K, but you’d damn well better make sure that you aren’t alone together, that you’re both stone cold sober, and that H knows that you’re out with her.

I can’t tell you what to do here, HaW. The longevity of your friendship with K—completely independent of your attraction to her—is a pretty good sign that the two of you would probably make a good couple. On the other hand, H’s been with you, supporting you and caring for you and vice versa. To quote a wise man: “You know, there’s a million fine looking women in the world, dude. But they don’t all bring you lasagna at work.” And while your relationship with H may not be the most passionate, passion can be built together.



The only thing I can say is that if you decide to end things with H, then do it as quickly and cleanly as possible. You can’t avoid hurting your fiancé when you leave, but you can avoid inflicting unnecessary pain.

Good luck.

Hey Doc.

I’m kinda new to your page and honestly I read only a handful of your letters and replies. So, the thing is: I still love my ex. And to make it all worse, she recently broke up with her boyfriend ‘cause she found out he was cheating.

To give you some background, me and her dated for about 3 years and broke up a year and 3 months ago. We had an amazing relationship that slowly began to go sideways as her mother didn’t really like me and was as protective as she could. She was always telling her daughter that she was too young to be in a serious relationship (we were 18 when we began dating) and that she should enjoy life more.

As if that weren’t bad enough, I wasn’t really the best person to be around. I had dysthymia (probably still do), which made me moody and a bit anti-social. So with time, she slowly began doubt if we should really stay together and consequently, I guess, her feelings towards me began to change. When we were about to get to the three years mark, we had a discussion and she decided that was it.

I never really got over her. I did date other girls but was never able to commit to them. Nothing got even close to the feeling I had for my ex and, to be completely honest, the same feeling never went away.

Three months after we broke up, I found out she was already dating someone. She went as far as to say she was deeply in love with him and for some reason was always posting pics of them on her social media. The thing is, when we dated, we would rarely do anything like that. Also, her boyfriend was a manipulative asshole who would always try to control her and make her do shit he wanted to. I know it may sound as something a bitter ex would say, but his cheating on her kind of proves my point, I hope.

On rare occasions throughout the year they were together, she would suddenly call or text me and say that she missed me or that she wanted me to know that what we had was special to her. It made me feel like shit, to be honest.

So, last week shit hit the fan and she discovered all of his fooling around. I was with her at the time as I was the one who alerted her that he might be cheating on her. (I know, a dick move.) People would constantly tell me he was doing something, but when a friend I trusted said it as well I got so pissed that I just told her about it. She’d then asked a mutual friend and he told her all about it.

And now I really just don’t know what to do with this situation. I got really mad at the guy for cheating on her. I got really mad that he broke her heart. But at the same time I felt a bit happy and relieved, even. She began to speak to me again and I’m a bit closer to her as I am helping her through it, no dishonorable intentions (at least not consciously, I guess).

I guess my question is: What the hell should I do? It’s the woman I love, with a broken heart and I’m so confused I don’t eve know how to react properly.

Second Time Around

Allow me to quote you a bit of wisdom that applies when dealing with women in a vulnerable state: “If you take sexual advantage of her, you’re going to burn in a very special level of hell. A level they reserve for child molesters and people who talk at the theater.”


OK, let me step that back for a second. I’ve been where you are, STA. There was a woman I dated who I was absolutely mad about, and when we broke up, I didn’t take it well. In fact, I didn’t get over her for years. I couldn’t really commit to the other women I dated, because I was still hoping for her to come back to me. It didn’t help that I was constantly picking at the scab - following her on social media and keeping track of her romantic adventures. Every mention of her boyfriend was a new form of self-flagellation, keeping the pain raw and open.

(This, incidentally, is one of the reasons why I advocate unfollowing or muting your ex on social media when you break up; you’ll never heal if you keep finding excuses to rip the wounds open.)

Eventually, she broke up with her boyfriend and we reconnected under the pretext that I was over her and ready to just be friends.



Which, as I’m sure you might guess, was a big fat, stinking lie. I wanted her back in the worst damn way and even though I knew better, I tried to pull the Platonic Best Friend Back Door Gambit. One night she found out that her ex had been cheating on her and I, classy dude that I was, decided that this was the best night for the two of us to go on a pub crawl to help ease her broken heart.

Some ill-advised make-outs and one very close call later and suddenly there’s this new level of awkwardness and distance between the two of us. Why? Because there I was, positioning myself as her friend and trying to take advantage of her emotional state for my own selfish desires. That’s not something a friend does, that’s something a selfish asshole does. It hurt her, it damaged our friendship and it set my progress back significantly. It was a really, really, bad idea on my part.

I tell you this so that you don’t make the same mistakes I did. Your ex, someone you still care for, is hurting. She’s had her heart broken by an asshole and needs a friend right now. Not a guy who’s hoping to get in her pants, not someone hoping to maneuver his way back into her heart. A friend. Someone she can trust to just be there for her without any ulterior motives.


Maybe you are that friend. But even if you are, let your ex set the pace. She knows what she needs more than anyone else does. So put it out there that you’re there to help if she needs it. But let her come to you. This about her and her needs, not any hopes you may harbor for the future.

Be the shoulder for her to cry on without judgement. Listen to her when and if she needs to talk. If she needs distance, let her have distance. If she needs company, give her company. If she needs to be kept busy, then you can help. But let her set the tone and the pace.

And remember: these interactions are not about you. These are not opportunities or dates. If you’re going to be a friend, then just be her friend until she’s better. And if you can’t do that, then you need to keep your distance until she’s not nursing her broken heart.



Good luck.

Dear Dr. NerdLove,

I’ll just get right to the point — my boyfriend of two years has started to resent everything he used to admire about me, and I feel like every interaction we have has the potential to become an argument over basically nothing.

I am a licensed attorney, and although I don’t currently practice law my education is what made my current career possible — I make very good money and I’m proud of my success in a male-dominated field. I am also not afraid to say that I am a very attractive woman and that I receive a lot of attention from men. My looks are by and large the first reason a man approaches me and wants to date me, but my relationships are almost always based on their respect for my intelligence, professional success, and love of beer and sports. My boyfriend used to tell people that when he met me, he found a unicorn.

He does not have a college degree, but makes a six-figure salary in his chosen profession. He is very smart and we share a lot of the same interests. Recently, we bought a house together, but here is where it gets sticky. For a variety of reasons, we agreed that I should buy the house on my own and keep it solely in my name. He is renting out the house he still owns, and pays for utilities and other small projects around our new house. I am fine with this arrangement and it was HIS suggestion that we do it this way.

Lately, we’ve been arguing a lot, and it almost always devolves into him throwing my education (or his lack thereof) in my face, and suggesting that I think I am better than him. (I have NEVER, EVER resorted to that line of argument and I unequivocally do not feel this way). He will also threaten to go back to “the house that he pays for” and will state that his opinion clearly doesn’t matter around here because this is “my” house, and I’m the breadwinner. Two weeks ago he flat-out said I make him feel inferior.

He also has a jealous streak, which I don’t mind in small doses, but he applies a pretty harsh double standard to our interactions with the opposite sex and is bothered by all of the men I have to deal with and have become friendly with through my job. I also recently found out that he had been texting another woman with pictures of half-naked Instagram girls and saying he’d like to recreate the photos with her as the star. He swears nothing happened, which I believe, but only because she wasn’t interested.

The worst part is this is exactly how my first marriage came to an end — even though my ex made the same salary as me, he often threw my success in my face and finally resorted to hitting strip clubs 3 times a week so he could find women who would “be nice to him” and “not make him feel insecure.”

I love my boyfriend more than I have ever loved anyone (including my first husband) and really believed that marriage and kids were in our future. But even on our best days, he refuses to discuss our issues and prefers to sweep things under the rug and say “tomorrow is a new day.” I also want to be clear that we have sex pretty much anytime he wants it, and I keep myself in excellent shape.

What is going on here and what should I do?????

Everyone Loves Unicorns Until They Don’t

There’re two possibilities here. The first is that you’re behaving in a way that hurts him and he doesn’t have the emotional intelligence to tell you instead of acting out. The other is that he’s an insecure butthead and he’s lashing out at you. Either way… well, breaking up with him is the best option.

Between you, me and the comments section: I’m more inclined to believe the second possibility. Here’s the thing about women who are “intimidating”—nine times out of 10, it’s because the guy tends to be insecure with someone who’s more accomplished than he is, because it threatens his status as a man. That’s not the behavior of a grown-ass man, nor is it something you need from a relationship. And, quite frankly, unless he decides to put on his big boy pants and deal with his issues, it’s not going to get better.


Part of the problem is that at first, he’s using your success as proof of how awesome he is. Here he is with this beautiful, accomplished woman who also likes beer and sports (and oh how rare that is! How lucky he is to have found this unicorn! *gag*) and isn’t it awesome how proud of you are he is and how totally not threatened he is by it all?

And then, whoops, no he’s actually not cool with all of it and he’s starting to smoulder with resentment and jealousy because he’s bought into toxic ideas about what it means to be a man. Because he doesn’t measure up to these arbitrary standards, he’s had his manhood taken from him… and he’s blaming you for it.

Let’s look at things objectively. Your boyfriend is jealous of your success and your accomplishments and throws them in your face like you’ve done something wrong. He continually threatens to leave for a place where he feels superior because of an arrangement the two of you agreed on, presumably in good faith. He doesn’t trust you and polices your relationship with other guys and co-workers.



That’s a whole lot of red flags right there. We may not be up to Soviet Military Parade levels of warning but this relationship has all the hallmarks of one that can turn abusive very quickly. Your boyfriend’s currently a walking example of #MasculinitySoFragile—the fact that you’re successful means that he’s less of a man. And as things continue, he’s going to start punishing you for the way he feels.

Take his not-so-surreptitious flirting (because that’s exactly what he’s doing). Part of the reason proposing to recreate photos of half-naked women on Instagram is because he’s looking to get his balls back by proving his manliness in other ways. By setting up these shoots (which, let’s be honest, he’s going to try to leverage into hook-ups… which is creepy as fuck, by the by) he’s putting himself in charge of a beautiful woman and asserting his masculinity that way. And if she happens to touch his penis in the course of said shoot… well, he’s just such a massive hunk of man, how could any woman resist?

And of course, you finding out is intended to hurt too. Now he gets to blame you for “making” him do it with your castrating ways.


I’m going to be honest: I don’t really hold out much hope for improvement. If he were willing to work on things in good faith, then maybe you could both pull this relationship out of its nosedive. I’d suggest some therapy for him personally and maybe some couple’s counseling so the two of you can find ways of discussing these issues and finding ways to work together to make things better.

But if all that’s going to happen is that he’s going to blame you and try to brush off suggestions of help? Then nothing’s going to get better, and your best bet is to end things with him.

So the only advice I have is to give him an ultimatum: either he talks to a counselor or he can go back to the house he pays for good.



I wish I had better advice for you. It’s clear that you love and care for him. But if he can’t handle not being the brightest star in the sky that is your relationship and he’s not willing to put in the work to improve things, then he’s just not right for you and you can’t love someone hard enough to magically fix them yourself.

Good luck.

Do you have experience with dealing with temptation in a relationship? Did you get a second chance with your ex? Share your thoughts and experiences in the comments and we’ll be back in two weeks with more of your dating questions.

Ask Dr. Nerdlove is Kotaku’s bi-weekly dating column, hosted by the one and only Harris O’Malley, AKA Dr. NerdLove. Got a question you’d like answered? Write doc@doctornerdlove.com and put “Kotaku” in the subject line.


Harris O’Malley is a writer and dating coach who provides geek dating advice at his blog Paging Dr. NerdLove and the Dr. NerdLove podcast. His new dating guide New Game+: The Geek’s Guide to Love, Sex and Dating is out now from Amazon, iTunes and everywhere fine books are sold He is also a regular guest at One Of Us.

He can be found dispensing snark and advice on Facebook and on Twitter at @DrNerdLove.

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